CAS 79831-76-8|Castanospermine

Introduction：Basic information about CAS 79831-76-8|Castanospermine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Castanospermine BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles36
6. Synonyms

Common Name	Castanospermine
CAS Number	79831-76-8	Molecular Weight	189.209
Density	1.5±0.1 g/cm3	Boiling Point	421.9±45.0 °C at 760 mmHg
Molecular Formula	C₈H₁₅NO₄	Melting Point	213-217 °C(lit.)
MSDS	ChineseUSA	Flash Point	267.6±27.4 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	castanospermine
Synonym	More Synonyms

Castanospermine BiologicalActivity

Description	Castanospermine inhibits all forms of α- and β-glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids).target：α- and β-glucosidases.IC 50: 1.2 uM [2] in vitro :Castanospermine, [(1 S,6S,7R,8R,8aR)-1 ,6,7,8-tetrahydroxyoctahydroindolizine]is a potent and specific inhibitor of mammalian and plant α-and β-D-glucosidases in vitro [1] in vivo: Experiments in vivo with castanospermine, an inhibitor of the glucosidases that convert protein N-linked high mannose carbohydrates to complex oligosaccharides, resulted in significant inhibition of tumor growth in nude mice.[3]
Related Catalog	Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Cancer
References	[1]. Bryan G, Anthony C et al. The structural basis of the inhibition of human glycosidases by castanospermine analogues. Biochem. J. (1990) 269, 227-231. [2]. Eisaku Tsujii et al. Nectrisine Is a Potent Inhibitor of a-Glucosidases, Demonstrating Activities Similarly at Enzyme and Cellular Levels. Biochemical and Biophysical Research Communications 220, 459-466 (1996) [3]. Pili R et al. The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, preventsangiogenesis, and inhibits tumor growth. Cancer Res. 1995 Jul 1;55(13):2920-6.

Description

Castanospermine inhibits all forms of α- and β-glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids).target：α- and β-glucosidases.IC 50: 1.2 uM [2] in vitro :Castanospermine, [(1 S,6S,7R,8R,8aR)-1 ,6,7,8-tetrahydroxyoctahydroindolizine]is a potent and specific inhibitor of mammalian and plant α-and β-D-glucosidases in vitro [1] in vivo: Experiments in vivo with castanospermine, an inhibitor of the glucosidases that convert protein N-linked high mannose carbohydrates to complex oligosaccharides, resulted in significant inhibition of tumor growth in nude mice.[3]

Related Catalog

Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Cancer

References

[1]. Bryan G, Anthony C et al. The structural basis of the inhibition of human glycosidases by castanospermine analogues. Biochem. J. (1990) 269, 227-231.

[2]. Eisaku Tsujii et al. Nectrisine Is a Potent Inhibitor of a-Glucosidases, Demonstrating Activities Similarly at Enzyme and Cellular Levels. Biochemical and Biophysical Research Communications 220, 459-466 (1996)

[3]. Pili R et al. The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, preventsangiogenesis, and inhibits tumor growth. Cancer Res. 1995 Jul 1;55(13):2920-6.

Chemical & Physical Properties

Density	1.5±0.1 g/cm3
Boiling Point	421.9±45.0 °C at 760 mmHg
Melting Point	213-217 °C(lit.)
Molecular Formula	C₈H₁₅NO₄
Molecular Weight	189.209
Flash Point	267.6±27.4 °C
Exact Mass	189.100113
PSA	84.16000
LogP	-1.61
Vapour Pressure	0.0±2.3 mmHg at 25°C
Index of Refraction	1.647
InChIKey	JDVVGAQPNNXQDW-TVNFTVLESA-N
SMILES	OC1CN2CCC(O)C2C(O)C1O
Storage condition	2-8°C
Water Solubility	1 M HCl: 20 mg/mL, clear, very faintly yellow

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302-H312-H332
Precautionary Statements	P280
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn: Harmful;Xi: Irritant;
Risk Phrases	20/21/22
Safety Phrases	S26-S36
RIDADR	NONH for all modes of transport
WGK Germany	3

Articles36

LMAN1 (ERGIC-53) is a potential carrier protein for matrix metalloproteinase-9 glycoprotein secretion.

Biochem. Biophys. Res. Commun. 464 , 685-91, (2015)

Matrix metalloproteinase-9 (MMP-9) is a secreted glycoprotein with a major role in shaping the extracellular matrix and a detailed understanding of the secretory mechanism could help identify methods ...

Evolution of polyphenols and organic acids during the fermentation of apple cider.

Biochem. J. 469(1) , 83-95, (2015)

Polyphenols and organic acids are important constitutes in the cider because they greatly contribute to organoleptic quality. The determination of their changes is important for monitoring the ferment...

Inhibitors of the tick-borne, hemorrhagic fever-associated flaviviruses.

Antimicrob. Agents Chemother. 58(6) , 3206-16, (2014)

No antiviral therapies are available for the tick-borne flaviviruses associated with hemorrhagic fevers: Kyasanur Forest disease virus (KFDV), both classical and the Alkhurma hemorrhagic fever virus (...

Synonyms

1,6,7,8-Indolizinetetrol, octahydro-, (1S,6S,7R,8R,8aR)-

Castanospermine

(1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol

Castanospermine,[1S-(1α,6β,7α,8β,8aβ)]-Octahydro-1,6,7,8-indolizinetetrol

(1S,6S,7R,8R,8aR)-Octahydroindolizine-1,6,7,8-tetrol

MFCD00017555

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